Lattice energetics and thermochemistry of phenyl acridine-9-carboxylates and 9-phenoxycarbonyl-10-methylacridinium trifluoromethanesulphonates

Zadykowicz, Beata; Krzymiński, Karol; Storoniak, Piotr; Błażejowski, Jerzy

doi:10.1007/s10973-010-0789-6

Cited by 9 publications

(9 citation statements)

References 44 publications

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“…Acridinium salts investigated (Scheme ) were synthesized starting from 2-methoxyacridine-9-carboxylic acid ( 1 − 3 : 2-methoxy-10-methyl-9-(phenoxycarbonyl)acridinium ( 1 ), 2-methoxy-10-methyl-9-[(2-methylphenoxy)carbonyl]acridinium ( 2 ), and 9-[(2-chlorophenoxy)carbonyl]-2-methoxy-10-methylacridinium ( 3 )) or acridine-9-carboxylic acid (Aldrich) ( 4 − 6 : 10-methyl-9-(phenoxycarbonyl)acridinium ( 4 ), 10-methyl-9-[(2-methylphenoxy)carbonyl]acridinium ( 5 ), and 9-[(2-chlorophenoxy)carbonyl]-10-methylacridinium ( 6 )) and the appropriate hydroxybenzene (Aldrich): phenol, 2-methylphenol, or 2-chlorophenol. ,, Detailed information concerning synthesis of the compounds and their analyses are given in the Supporting Information. Physicochemical properties concerning derivatives 4 − 6 are reported in some of our other papers: spectral, thermal , and NMR ( 1 H + 13 C) . Crystallographic data relevant to some of the derivatives discussed here are given elsewhere. − ,− …”

Section: Methodsmentioning

confidence: 99%

“…Physicochemical properties concerning derivatives 4 − 6 are reported in some of our other papers: spectral, thermal , and NMR ( 1 H + 13 C) . Crystallographic data relevant to some of the derivatives discussed here are given elsewhere. − ,− …”

Section: Methodsmentioning

confidence: 99%

“…MS analyses were performed using a Fennigan LCQ Deca Surveyor LC/MS/MS spectrometer (electrospray ionization) . Mass spectra were acquired in the positive polarity mode in the m / z scan range of 100−600 (N 2 sheath gas), with the source, capillary, and trap voltages set at 5 kV, 17 V, and 10 V, respectively.…”

Section: Methodsmentioning

confidence: 99%

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Chemiluminogenic Properties of 10-Methyl-9-(phenoxycarbonyl)acridinium Cations in Organic Environments

et al. 2010

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The chemiluminogenic (CL) properties of aryl esters of 9-carboxy-10-methylacridinium acid and 9-carboxy-2-methoxy-10-methylacridinium acid (AE), variously substituted in the benzene ring (2-H, 2-CH(3), 2-Cl) were investigated in aliphatic alcohols, acetonitrile, and dimethyl sulfoxide in the presence of hydrogen peroxide and different bases-potassium hydroxide, tetra-n-butylammonium hydroxide, and 1,8-diazabicyclo[5.4.0]undec-7-ene. The dependence of their CL properties (decay rate constants (k(CL)) and relative efficiencies (RE)) on solvent parameters, the nature and concentration of base, as well as H(2)O(2) concentration were investigated. Comparison of the various AE revealed that substituents at the benzene ring strongly influence the reaction kinetics, while 2-OCH(3) substitution of the acridine nucleus is manifested, in general, by a red shift in the emission spectrum and slight increase in CL efficiency. The values of k(CL) depend linearly on polarity and acid-base properties of solvents as well as on concentration of bases (over certain concentration ranges) and demonstrate a nonlinear dependence on H(2)O(2) concentration. RE values depend on solvent polarity and nucleophilicity but are rather weakly dependent on base and oxidant concentrations. The CL properties of the above systems are discussed in the context of their physicochemical features gained from fluorescence spectroscopy, spectrophotometric titration, MS, and HPLC. Electronically excited 10-methyl-9-acridinones are the light-emitting entities in both organic and aqueous environments. It was also found that the tendency for an unwanted side-process, the production of a pseudobase form of AE, to take place was similar in alcoholic and aqueous media, although 2-methoxy ring-substituted derivatives seemed to be less susceptible to this dark-type conversion. On the basis of these results new CL systems are postulated that are more efficient than their aqueous counterparts.

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Section: Methodsmentioning

confidence: 99%

Section: Methodsmentioning

confidence: 99%

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Chemiluminogenic Properties of 10-Methyl-9-(phenoxycarbonyl)acridinium Cations in Organic Environments

et al. 2010

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“…Although the methods for the preparation of 10-substituted 9-(phenoxycarbonyl)acridinium salts have been described in the literature, 22,[25][26][27][28][29][30][31][32]36 a few remarks concerning the compounds investigated here should be made (their synthesis and spectroscopic analyses are reported in the ESI †). To ensure a clean and effective synthesis of XAEs (Scheme 1), their immediate precursors, substituted 9-[( phenoxy)carbonyl]acridines, must be obtained in high yield and purity.…”

Section: Synthetic Considerationsmentioning

confidence: 99%

“…[25][26][27][28][29][30][31] On the other hand, applying differential scanning calorimetry methods to study their thermal behavior enabled us to assess important physicochemical parameterssuch as the crystal lattice energy, enthalpies of volatilization and formation and others. 32 In this work, we present investigations of the luminogenic properties of XAEs, including theoretical, structural and physicochemical studies on the liquid phase. Since most of the compounds presented here express higher emission efficiencies than their alkyl analogues, 22 we attempt to reveal the possible reason(s) for this phenomenon, including analyses of the post-CL reaction mixtures.…”

Section: Introductionmentioning

confidence: 99%

Effective chemiluminogenic systems based on acridinium esters bearing substituents of various electronic and steric properties

et al. 2016

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A series of 10-methyl-9-(phenoxycarbonyl)acridinium trifluoromethanesulfonates (XAEs), bearing substituents of various characteristics in the lateral benzene ring (2-halogen, 2,6-dihalogen, 2-trifluoromethyl, 2-nitro, 2-methoxy, 3-halogen and 4-halogen) were synthesized with high yields, identified and subjected to a physicochemical and theoretical investigation. The main task of the work was to assess the mechanism and optimal conditions of light emission in various liquid systems based on the above salts in order to evaluate their potential usefulness as chemiluminescence (CL) labels and indicators in ultra-sensitive analyses. Density functional theory (DFT) calculations were performed to investigate the detailed mechanism of the oxidation of 9-substituted 10-methylacridinium cations involved in XAEs by hydrogen peroxide in alkaline media. Three general pathways were drawn, which are termed the "light path" (chemiluminogenic) and there were two "dark paths" (non-chemiluminogenic): hydrolytic and "pseudobase". The CL time profiles, triggered in alkaline solutions containing hydrogen peroxide, enabled us to establish crucial physicochemical parameters, including pseudo-first order kinetic constants of CL decay and relative efficiencies of emission. In order to optimize the systems' luminogenic performance, different bases, such as sodium hydroxide, tetrabutylammonium hydroxide (TBAOH) and 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU), as well as enhancers, such as cationic, zwitterionic and neutral surfactants (cetyltrimethylammonium chloride (CTAC), N,N-dimethyldodecylammonio-1,3-propane sulfonate (DDAPS) and Triton X-100, respectively) were tested. The results revealed the optimal CL systems, which enabled us to obtain substantially higher emissions than typical ones, based on acridinium esters or luminol. The derived parameters, characterizing the potential utility of the acridinium esters, such as stability in aqueous environments and usefulness (the product of emission efficiency and stability at a given pH), enabled us to reveal the best candidates and their practical applications. The post-reaction mixtures, analyzed by means of chromatography (RP-HPLC) and mass spectrometry (ESI-MS), allowed us to verify the occurrence and population of the products that were theoretically predicted, i.e. 10-methyl-9-acridinone (NMAON), 10-methylacridinium-9-carboxylic acid (NMACA) and substituted phenols (RPhOHs).

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Thermal stabilities of some benzaldehyde 2,4-dinitrophenylhydrazones

Cusu

Musuc

Oancea

2011

J Therm Anal Calorim

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Lattice energetics and thermochemistry of phenyl acridine-9-carboxylates and 9-phenoxycarbonyl-10-methylacridinium trifluoromethanesulphonates

Cited by 9 publications

References 44 publications

Chemiluminogenic Properties of 10-Methyl-9-(phenoxycarbonyl)acridinium Cations in Organic Environments

Chemiluminogenic Properties of 10-Methyl-9-(phenoxycarbonyl)acridinium Cations in Organic Environments

Effective chemiluminogenic systems based on acridinium esters bearing substituents of various electronic and steric properties

Thermal stabilities of some benzaldehyde 2,4-dinitrophenylhydrazones

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